6-METHYLINDOLE-3-CARBOXALDEHYDE Chemical Properties

Melting point:

185-189°C

Boiling point:

339.3±22.0 °C(Predicted)

Density 

1.226±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

15.86±0.30(Predicted)

Appearance

Light yellow to yellow Solid

Sensitive 

Air Sensitive

BRN 

386914

CAS DataBase Reference

4771-49-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36

Hazard Note 

Irritant

HS Code 

2933998090

MSDS

• Language:English Provider:ALFA

6-METHYLINDOLE-3-CARBOXALDEHYDE Usage And Synthesis

Uses

6-Methylindole-3-carboxaldehyde is an indole compound that can be prepared by the C3-formylation of indole with formaldehyde and ammonia catalysed by iron in air. The substance can also be used to prepare other nitrogen-containing heterocyclic compounds, which are widely used in chemical manufacturing, medicine, dyes and luminescent materials.

Synthesis

The general procedure for the synthesis of 6-methylindole-3-carbaldehyde from 6-methylindole and N,N-dimethylformamide is as follows: 1. Synthesis of indole derivatives 1) Synthesis of 3-cyanoindole derivatives Formylation of the 3-position of the corresponding indole was carried out in dimethylformamide (using Vilsmeier's method) using phosphorus trichloride. Subsequently, nine 6-methylindole-3-carboxaldehydes were prepared by cyanidation achieved by dehydration reaction with hydroxylamine in sodium formate and formic acid. Next, the coupling reaction with ethyl 4-fluorobenzoate was carried out in a dimethyl sulfoxide solution of potassium fluoride, amino acids and 18-crown-6-ether. Finally, hydrolysis was carried out with lithium hydroxide, completing a total of 4 steps of reaction. 2) Preparation of XO-CH172 and XO-CH183 (R is 2-methyl or 5-methoxy, respectively) from step (2) using commercially available corresponding aldehydes. 1) Synthesis of XO-CH200 Under argon protection, 6-methylindole (1.004 g, 7.62 mmol) was dissolved in dimethylformamide (10 mL), and phosphorus trichloride (2 mL) was slowly added to this solution under ice bath cooling. The reaction mixture was stirred at room temperature for 1.5 hours. An aqueous sodium hydroxide solution (5 g/15 mL) was added dropwise to the reaction mixture under ice bath cooling. Subsequently, the mixture was heated to reflux for 1.5 hours. Cooled again in an ice bath, water was added to the reaction mixture and the pH was adjusted to 3 with concentrated hydrochloric acid. the solid product was collected by filtration and dried under reduced pressure at 60 °C to give XO-CH180 in light brown solid form (1.14 g, 94% yield).

References

[1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 24, p. 5696 - 5705
[2] Patent: EP1932833, 2008, A1. Location in patent: Page/Page column 15; 19
[3] Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 864 - 868
[4] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 776 - 783
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1301 - 1305

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